phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 1144104-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8S,8aR)-6-[[(2R,4aR,6R,7S,8S,8aR)-2-phenyl-8-phenylmethoxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy]-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 1144104-37-9
• 化学式: C₅₃H₅₂O₁₀S
• 分子量: 881.056
• InChiKey: SLJHIERJSAAVNF-ZVYCLJCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以62%的产率得到2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-D-mannopyranoside
  参考文献：
  名称：

  β-(1→2)-连接寡甘露糖苷的合成

  摘要：

  β-(1→2)-连接的寡甘露糖苷构成了一类重要的碳水化合物结构，位于几种念珠菌属的细胞表面，包括白色念珠菌。由于这些化合物的免疫刺激特性，它们合成的放大是相关的。在本文中，β-(1→2)-连接的寡甘露糖苷的高度立体选择性合成是通过进一步开发和修改文献中先前描述的方法来进行的。除了合成完全脱保护的 β-(1→2)-连接的甘露二糖和甘露三糖之外，还介绍了对寡糖核心的一些初步修饰，从而产生了具有生物潜力的紧密类似物。完全脱保护的产品形成了筛选白色念珠菌的潜在目标，也可能导致疫苗开发的新模型结构。

  DOI：

  10.1002/ejoc.200801024
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 三氟甲磺酸酐 、 BSP 、 sodium hydride 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

  摘要：

  Phosphorylated beta-(1 -> 2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated beta-(1 -> 2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.10.017

文献信息

• Fully deprotected β-(1→2)-mannotetraose forms a contorted α-helix in solution: convergent synthesis and conformational characterization by NMR and DFT
  作者：Filip S. Ekholm、Jari Sinkkonen、Reko Leino

  DOI：10.1039/b9nj00702d

  日期：——

  β-(1→2)-linked oligomannosides, found in the cell wall of Candida albicans, are promising structures for the development of C. albicans vaccines. Considerable effort in recent years has been devoted to the synthesis of these carbohydrate structures. As a result, several successful synthetic methodologies based on linear approaches have emerged. Here, we demonstrate that a fully deprotected β-(1→2)-linked

  在白色念珠菌的细胞壁中发现的β-（1→2）-连接的寡甘露糖苷是有发展前途的结构C。白色念珠菌疫苗。近年来，已经致力于这些碳水化合物结构的合成。结果，出现了几种基于线性方法的成功的合成方法。在这里，我们证明了完全脱保护的β-（1→2）-连接甘露糖也可以通过两个适当保护的二糖的汇聚直接偶联方便地构建。与以前发布的方法相比，这种改进的方法具有多个优点。达到较大的寡糖所需的步骤数减少了，而当用两种二糖进行关键的糖基化步骤时，保留了高选择性，本文提供了β-（1→2）-甘露糖 从以下步骤开始，在16个步骤中总收益率为4.2％ D-甘露糖。另外，报道了通过NMR光谱对产物的完整结构表征。在最终产品的构象研究中，将2D-NOESY与使用栖息软件。获得的实验结果证实了溶液中这些寡糖先前预测的扭曲的α-螺旋结构。作为构象研究的高潮，使用DFT通过分子建模构建了模型，并且发现最小能量构象与实验结果完全吻合。迄今
• Synthesis of β-(1→2)-Linked Oligomannosides
  作者：Monika Poláková、Mattias U. Roslund、Filip S. Ekholm、Tiina Saloranta、Reko Leino

  DOI：10.1002/ejoc.200801024

  日期：2009.2

  β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of β-(1→2)-linked oligomannosides was performed by further development

  β-(1→2)-连接的寡甘露糖苷构成了一类重要的碳水化合物结构，位于几种念珠菌属的细胞表面，包括白色念珠菌。由于这些化合物的免疫刺激特性，它们合成的放大是相关的。在本文中，β-(1→2)-连接的寡甘露糖苷的高度立体选择性合成是通过进一步开发和修改文献中先前描述的方法来进行的。除了合成完全脱保护的 β-(1→2)-连接的甘露二糖和甘露三糖之外，还介绍了对寡糖核心的一些初步修饰，从而产生了具有生物潜力的紧密类似物。完全脱保护的产品形成了筛选白色念珠菌的潜在目标，也可能导致疫苗开发的新模型结构。
• Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides
  作者：Jani Rahkila、Filip S. Ekholm、Rajib Panchadhayee、Ana Ardá、Francisco Javier Cañada、Jesús Jiménez-Barbero、Reko Leino

  DOI：10.1016/j.carres.2013.10.017

  日期：2014.1

  Phosphorylated beta-(1 -> 2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated beta-(1 -> 2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.